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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Spacious 2BR Condo + Free On-site Parking
2 bedrooms, 2 beds, 2 private bathrooms
26–31 Aug
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4.95 out of 5 average rating, 218 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.92 out of 5 average rating, 26 reviews, 4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
Home in Chicago
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
New place to stay, 4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Aug
Top guest favourite
Rooms in Chicago
Historic North Park home
4.97 out of 5 average rating, 117 reviews, 3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 126 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Flat in Chicago
Duplex in Bucktown
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
4.95 out of 5 average rating, 84 reviews, 2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.95 out of 5 average rating, 104 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
4.96 out of 5 average rating, 305 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
15–20 Aug
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
5.0 out of 5 average rating, 56 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Nov
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
New place to stay, 3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Chicago
Big house in the BEST Location!
4.98 out of 5 average rating, 62 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
Top guest favourite
Room in Chicago
Spacious garden level suite
4.96 out of 5 average rating, 317 reviews, 1 queen bed, 1 bathroom
10–15 Nov
Top guest favourite
Flat in Chicago
Designer CuratedVintage Condo in Popular West Town
4.94 out of 5 average rating, 252 reviews, 2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
Guest favourite
Room in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
4.9 out of 5 average rating, 49 reviews, 1 bed, 1 bathroom
24–29 Oct
Flat in Chicago
The Clubhouse at Wrigley | Sleeps 10
New place to stay, 4 bedrooms, 6 beds, 3.5 bathrooms
24–29 Aug
Flat in Chicago
Kasa Lake Shore Chicago | Studio Queen
New place to stay, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug